English Master Dr. Cunningham is the Lawrenceville School's Dean of Faculty.

In addition to his teaching duties, Cunningham has been the School's Third Form English Curriculum Coordinator, Acting Chair of the English department, Chair of the Discipline Committee, and a member of numerous other School committees during his nine years at Lawrenceville. His efforts as head coach of the Big Red girls' varsity cross country team earned him Coach of the Year awards from the Trenton Times, Trentonian, and Star-Ledger in 2011.

Cunningham received his A.B. in Modern Thought and Literature, Phi Beta Kappa, from Stanford University and his Ph.D. in Literature from Duke University. His poetry, criticism, and reviews have appeared in many magazines and anthologies, including Slate, Iowa Review, Best New Poets 2006, Southwest Review, Ninth Letter, Black Warrior Review, Court Green, Cincinnati Review, Poetry International, Meridian, River Styx, Notre Dame Review, Smartish Pace, Western Humanities Review, Cimarron Review, Arizona Quarterly, Mississippi Quarterly. Twice nominated for a Pushcart Prize, Cunningham has completed a collection of poetry, No Stranger but Ourself, and is working on a book-length sequence, Mr. Anderson.

Before joining Lawrenceville, Cunningham taught at Princeton Day School, Stuart Country Day School, and Montclair Kimberly Academy. He was also an adjunct professor at Rider University and Mercer County Community College.